Jenny's Journey
by Riana Salvatore
Summary: Upon returning to say goodbye to Elena, Jeremy brings up something that his bothering him for a while. He's transgendered. Will a certain witch be able to help him be the girl he wants to be?
1. Chapter 1

I knew for a long time that I was never normal. I lost my parents when I was 15. I lost two girlfriends before my 16th birthday and lost my aunt and uncle from different sides not that long after. I got dumped by my 3rd girlfriend because I was cheating on her with the ghost of my 2nd. I almost got killed by a crazy psychopath and because of it was sent away from home. My guardian became a crazed killer before being killed with my sister being turned into a vampire. I became a vampire hunter and tried to kill my sister before I was killed and finally brought back to life. So I guess you can definitely say that I'm not normal.

And before all that, there was always an emptiness inside of me. I tried different ways of coping with it. I tried using drugs. I tried putting myself into vampire killing as a distraction. That was what I was doing now. I even thought about actually going to art school, but I wasn't sure if that would help. I liked girls, but I always wondered what it would be like to be one: to wear pretty clothes, to wear makeup, maybe even have a child as in have one. I had only ever told one person and that my girlfriend Anna. She was actually going to help me by compelling a doctor to give me hormones, or possibly even surgery, but then her mom died and then she died and nothing ever came from it.

I was scared to do anything about it. I regularly fought vampires, but I was scared to do anything towards becoming a girl. I didn't know what anyone else would think about it. I knew that since this was a supernatural world that I probably could even do it without science. I could use magic. I then got a phone call. It was from Alaric.

"Hi. I heard about the wedding. I'm sorry I missed it." I stated.

"There was no wedding." He replied. "Jo is dead."

"What happened?" I asked.

"Kai came back and killed her along with the rest of the Gemini Coven." He explained. "The good news is that managed to kill him as well, but that's not why I'm calling."

"Why are you calling?" I asked in concern. I wondered if there was more bad news.

"It's about Elena." He stated. "She took the cure."

"How is that even possible?" I questioned in confusion. "The cure was destroyed when Amara died."

"Before Bonnie came back, she grabbed it out of Silas's tomb." He told me. "Anyway, before Kai died, he put a curse on Elena."

"She what happened? Is she dead?" I inquired.

"No, she's technically alive." He answered. "The only thing is she's unconscious and she can't wake up until Bonnie dies. She's trapped in a state of limbo."

"So what are you doing about it?" I asked. I hoped that they weren't thinking of letting Bonnie die.

"We're going to let Bonnie live her life." Alaric declared. "We're basically going to keep her body safe somewhere, but we're holding a wake for her, and you need to be here."

"Okay, I'll get on the first plane there." I promised. "Don't start without me."

When I got there, everyone was in the Salvatore boarding house.

"So apparently the spell allows Elena to enter the mind of anyone that touches her." Alaric told me. That didn't seem like something Kai would do. "It's how we're going to say goodbye. Since you're her brother, you should go first."

I slowly walked over to her and grabbed her hand. It was warm. I needed to work on telling people and I supposed it was a good place to start especially since no one else would know about it. I found that we were at the old house.

"Jeremy, it's good to see you." She said as she gave me a hug.

"Elena, there's something that I need to tell you." I explained. I decided to just let it out. "I want to be a girl."

"I know." She replied. "I found out as soon as you touched my hand. I can control what this place looks like. Do you want to see what you'd look like as a girl?"

"I guess." I responded in a surprise. Suddenly she was taller than me. I looked in the mirror and I saw a girl with blonde hair wearing a white dress looking back at me. I was so pretty. "Wow."

I covered my mouth as a soft voice came out.

"So what do you want me to call you?" She asked.

"Jenny." I answered. I had long thought about the name. Even though I was basically just in a dream, it was still amazing.

"Okay, Jenny, I want you to be who you want to be." She replied. "That's why you need to tell everyone. Bonnie might even be able to help you with it."

"I'm scared." I admitted. "I don't know what they'll say about it."

"Jenny, these people love you. They won't care about something like this." She pointed out. "The worst that will probably happen is Damon making a snarky joke. You should be happy. Plus you could be the person that you want to be. Maybe you could even go to Whitmore."

I then let go of her and felt myself back in my own body. It was pretty depressing after seeing what I had just seen. Elena was right. I wouldn't feel any better unless I let myself be me. I needed to let myself be Jenny.

I decided that the first thing that I would do would be to let everyone else take their turns. Damon was going to go last. I had no idea what he would be like without her. The only reason that he was really tolerable was because of his love for my sister. I really hoped that he would be okay. As much as I hated to admit it, I cared about Damon.

"So what are we going to do with her now?" Matt asked. "We can't just keep her here while she still has the cure in her."

"That's why we're going to keep her in the family crypt." Damon stated. "We'll seal it off so no one can get there and whenever Bonnie dies, the seal will be broken."

"Wait." I interrupted. Everyone looked at me. "Before you do that, there's something that I wanted to tell you guys. This isn't easy for me, but I want to be a girl."

"I knew that you really liked guys." Damon remarked.

"I don't like guys, I still like girls, but I'm transgendered." I explained. "Elena told me that I should tell you guys about it and she even showed me what I would look like as a girl."

"So what are you going to do about it then?" Stefan asked.

"I was hoping that Bonnie might be able to use a spell for that." I admitted.

"I don't know any spells for that." Bonnie stated. I frowned. "But I can probably find one. Just let me do this first and then I'll get to work on it."

"Well you can send me a picture when you're done." Tyler stated. "I think I'm going to get out of here for good. Now that I'm a werewolf again, I need to move on and I want to see about starting a family."

We then went to the crypt. Once she was inside, we stepped out and watched as Bonnie began to work on the seal. I just hoped that she would be able to really see the real me. Even though I did want to be able to have a child, I also kind of wanted to be able to always look the same. I wanted to be that beautiful girl forever. I knew it was selfish, but at the same time, I was also doing it for Elena.

"So how was art school?" Matt asked me. I couldn't tell if he was comfortable talking about it or not.

"I didn't actually go to art school." I admitted. "I was looking for vampires to kill."

"So how long have you been like this?" He questioned.

"It was actually before my parents died." I explained. "I just never said anything about it."

"Did Vicki know?" He asked me.

"No. The only person that I ever told was Anna." I declared.

"I'm going to start looking through the grimoires to see if I can find anything." Bonnie stated. "I'll let you know when I do."

"Maybe I should come with you." I replied. "It'll move faster."

We then went back to her house and began to look through the books.

"So do you want me to call you something else?" She inquired.

"Jenny. My name is Jenny." I stated. "I really appreciate you doing this for me. I don't know how I'll be able to repay you."

"You don't have to repay me. I went to be able to help you with there, but there is something that you should probably know. I can't be certain, but I imagine the spell with change you on the genetic level, which means that you'll probably have a period and you'll probably be able to get pregnant."

"Well I'm not going to be having sex with guys, but that's one of the reasons that I want it." I said. "I want to really experience being a girl and I can't do that the medical way."

"Okay, I found the spell." She replied. "It says that you need to think about what you want to look like."

I focused on the image from before. I was really excited about it. My dream was about to come true. Bonnie began to chant and I couldn't help but feel myself losing consciousness. I hoped it was part of the spell.

I then felt myself slowly regaining consciousness. I was still wearing the same clothes, but they felt looser and my hair was longer. I felt two small lumps protruding from my chest and an emptiness between my legs. The spell had worked. I was a girl.

So I wanted to write a story about a transgender character and I decided on Jeremy and figured it could explain a lot of his angst. Jenny is played by Chloe Moretz. So what's going to happen next? How will be things be different? Please don't forget to review.


	2. Chapter 2

I then felt myself slowly regaining consciousness. I was still wearing the same clothes, but they felt looser and my hair was longer. I felt two small lumps protruding from my chest and an emptiness between my legs. The spell had worked. I was a girl.

Well it hadn't entirely worked. The one thing that hadn't changed was my clothes. As such, I was left with very baggy clothes that would have probably down if I stood up. I decided just to button my buttons. It covered enough for the moment, but I would have to address the problem soon.

"Can I have something to wear?" I asked the witch.

"It looks like we have to get you some of your own clothes." She stated.

"You should get Caroline over here." I suggested. "She loves this kind of stuff."

So in a short amount of time, we were at a local boutique. It was then that Caroline started to fill me in on things. On the same day that I had left, her mom died and it caused her to turn off her humanity. Stefan's nephew Zach also had a long-lost daughter named Sarah. Caroline had threatened her which got Stefan to turn off his own humanity. In order to get Stefan's back, they brought back Stefan and Damon's mother from this prison world and left Kai, which was why he was so angry and then Stefan got Caroline to turn hers back on. I had forgotten how much could happen in a few months.

"Alright, so the first that we need to do is get you fitted." Caroline stated. "You need to know you bra and you size in general."

She then took me to the counter and to the clerk.

"Hi, my friend here has lost a little bit weight lately and needs to be measured." She said. That was an understatement. I probably had lost at least 80 pounds.

Caroline bought me a lot of clothes, as in a lot of clothes. I wasn't sure how we were going to get them all into her car to be honest.

"Are you sure that I need this much clothes?" I questioned.

"You have a lot to learn about being a girl." She remarked. "The first rule is that a girl can never have too much clothes. Now we need to find you the right outfit for your party."

"Party?" I mimicked.

"We have to probably introduce you to the world." She explained. Well, being friends with Caroline was going to be different. "You have to let me teach you how to curl your hair. You know Elena will probably be so jealous when she wakes up."

"You know it sucks that I'm not going to be able to see her ever again." I stated. "Well I might when I'm old unless I die before Bonnie."

"We don't know what the future holds, Jenny." She pointed out. "Bonnie could die tomorrow or we could find some way to break the spell. We don't know what's going to happen."

"I guess you're right." I admitted.

"Of course I am. I'm always right." She replied. I couldn't help but giggle at that. "So we need to talk about your future. You should come to Whitmore. You can stay with Bonnie and me."

"I'm pretty sure that I missed the deadline to apply." I pointed out. "Besides, even if I could apply, I probably wouldn't even get in, and there's the fact that I'm not supposed to be a girl."

"You forget that compulsion can solve all of those problems." She remarked. "The least that you can do is give college a try. I think that you'll be able to find something that you like. Plus maybe you could meet a guy."

"Caroline, I still like girls." I pointed. "I changed my sex, not my sexuality."

"Well you could probably meet a girl then." She declared. "Oh and by the way, I need to school you on chick flicks. It's a good thing that we can have the whole summer to work with."

"Yay." I replied unenthusiastically.

That night was my party. Caroline had the idea for me to wear a white dress like I was a debutante. I thought I looked like I was getting married. All that was missing was the veil. Matt was going to take me downstairs.

"So how do I look?" I asked him.

"Well you look better than I thought you would." He admitted. I playfully shoved him. One side effect from the change was that I was no longer a Hunter because apparently only men could be Hunters. I couldn't believe that the witches were so sexist. Women could be badasses too. Caroline was proof of that. I would have to get used to that.

"I want my ring back." I stated. "I'm no longer supernatural and it is mine after all."

When I got down to the party, I quickly found that my tolerance for alcohol was a lot lower than it was before, which was not surprising considering my smaller body, but I was drunk after only one glass of Jack. I found out that I wanted to dance. I wanted to dance to this Demi Lovato song. I hadn't listened to her in a while, but it sounded nice, even though I wasn't sure whether or not it was just because I was drunk.

By the end of the night, everything was blurry. I was in Stefan's arms as he took me to one of the bedrooms.

"Where are we going?" I asked.

"I'm taking you to bed." He explained.

"I really don't feel so good." I replied "I'm gonna hurl."

He rushed me to the bathroom and I began to empty my stomach into it. I felt Stefan's hands on hair so I wouldn't get vomit in it.

"Thanks." I replied before I resumed hurling. I knew that I wasn't going to drink again for a while, or at least not as much.

A few months later, I parked Elena's car in a resident parking spot at Whitmore University. After several months, I was getting the hang of being a girl. One thing that I learned was that having a period sucked. It fucking sucked. I was all moody and bloated and I really underestimated what it was like to have one. I thought that Elena was just using her period as an excuse to be a bitch, but I realized that it wasn't the case. I was pretty sure that I made Stefan's life a living hell during my first period.

I stepped out of the car. It was the first time that I really had a car of my own. Elena wouldn't be using it for a while. I had a few of Elena's old things, but her clothes weren't something that I could keep since we were different sizes. I was wearing a long-sleeved black tee shirt with a denim miniskirt and black boots. I also had a heart necklace with some vervain in it because while I didn't know of any vampires on campus, it was better to be safe than sorry since I could be compelled again.

One thing different about this year was that Ric was not returning to his job as Occult Studies professor. He had actually left town and went to move on with his life. Hopefully, he was going somewhere away from vampires. He had lost more lovers than I had.

It was actually my first time on campus. I never thought that I would make it to college. I still didn't know how I would do, but I was smart and I probably could succeed if I tried. I was majoring in graphic design, which basically fell under the category of art.

I took the key to the room and turned the key and Caroline gave me a big hug.

"It's good to see you too, Care." I stated. "Now can please let me go? I like my spine the way it is."

"So you know what's interesting is that we're all in different years." Bonnie remarked. She was only a sophomore because of all of the time that she missed being in other worlds. "So what are you majoring in?"

"I'm doing Art with a minor in History." I explained. "I'm not sure that I want to be here, though."

"Give it some time." Caroline told me. "Tonight, we're going to take you to a sorority party."

"Something tells me that I shouldn't be so close to alcohol." I stated.

"We'll make sure that nothing happens to you." The blonde promised.

"I still have a lot of things to do." I pointed out. "I need to go to the bookstore. I need to go and get my student ID. I need to do a lot of things."

"You're going to the party if I have to make you." Caroline stated. I sighed because I knew she was very capable of doing so.

I headed down to the bookstore. I hadn't actually considered how I was going to be able to carry all of the books. However, I was pretty sure that hard textbooks were on their way out. I began to look down the aisles for the books that I needed. I was taking Biology this semester. I really hoped that I wouldn't have to dissect anything. I knew that I had beheaded a hybrid and killed multiple vampires, but I did not like the idea of taking dead animals apart. Why did I even need to take it if I was an art major?

"Do you need any help with anything?" A tall, thin guy in a fraternity shirt asked me. I wasn't sure if he worked there or not. I also wasn't sure if he was into me or not.

"I'm trying to find my books." I explained.

"Well, you're in the right place for that." He quipped. I didn't laugh. "What classes are you in?"

He guided me down the aisles as I picked up the four books that I needed. They were all paperback, so I would be able to carry them and I had worked out a little bit so I wasn't a complete weakling.

"So I'm Mark. What's your name?" He asked.

"Jenny." I stated as we headed to the register.

"Do you think I can have your number?" He questioned.

"No, I can assure that it's not going to happen because I'm gay." I stated. It probably wouldn't be the last time that I had to tell a guy that I was a lesbian. I didn't want to start dressing like a lesbian because part of wanting to be a girl was wanting to be feminine. I liked that my hair was long, even though it sometimes blew in my face. I liked being able to wear skirts, even though I had to watch how sat down and could end showing things I didn't want to if I fell over.

"Oh, well that's cool." He replied. "You know I have a sister who's a lesbian. I could introduce you to her if you want."

"I think I'm good." I responded before I paid for my books. All together, they were a bit heavy, but I could carry them. It did make the walk back a little bit harder and I was really sweaty by the time that I got back to the room.

"Okay, walking across campus in this heat is not fun." I replied.

"I've never really had to deal with it." Bonnie admitted. "Summer was over both times that I started here."

"Well I think I'm going to go get a shower." I stated.

I couldn't help but be a little bit nervous because it was the first time I had ever used a public bathroom. Last year, this wouldn't have been the case because the room had its own bathroom, but there was a new room this year. I grabbed a towel and my bath kit and headed down the hall.

The bathroom was empty to my knowledge when I entered. I went behind one of the curtains. Being the public bathroom, I couldn't help but think of this movie called _Pitch Perfect_ that Caroline had showed me. There was a scene where one of the girls came into the lead's shower while both of them were naked. I was kind of mad that they didn't end up together, because how could you not want to be with someone after having that kind of moment with them? Well, I wouldn't want it to happen to me. I began to undress and turn on the tap.

The water felt so good when it touched my skin. It kind of mad me want to touch myself. I had experimented a little bit with masturbation. I didn't have any particular fantasies. I did know that it wasn't the time for that at the moment. I just needed to wash up quickly.

It took a little bit longer than it would have because it took longer to wash my hair. I was wondering if I should die it brown to look more like Elena's.

I came out of the shower and began to dry off before wrapping the towel around my body. I picked up my clothes and my kit and pulled back the curtain and stepped out to see something that I didn't expect to see. There was a naked, dry redhead in front of me.

"Hello." She said with a smile.

"Um, hi." I greeted her with a blush. "Is there any reason why you're naked?"

"I was about to get in the shower." She stated. "I'm Dylan. What's your name?"

"Jenny." I answered. "So, I should probably let you get in the shower."

"Well if you ever want to talk some more, I'm in 208." She declared. That was the room next to ours. "By the way, what do you think?"

She was a little bit shorter than me. She appeared to have the same size chest as I did, maybe slightly smaller. She had a tattoo of a crescent on her thigh. She was definitely hot, though."

"You look really good." I stated. I then walked out of the bathroom because I couldn't take any more of it.

So Jenny's beginning to learn about being a girl and she met her love interest. Dylan is played by Haley Ramm. Please don't forget to review.


End file.
